Cheshire, MA Area Hotels

Name by letter
Click the letter below to show only hotels starting with that letter. You may also type all or part of a hotel name in the box above to find all hotels that contain the entered name. A B C D E F G H I J K L M N O P Q R S T U V W X Y Z ALL
Hotel Preferences
Meal Plans Offered
Hotel Type
Number of Rooms

Set Search Radius
0 miles
Drag or click to zoom in or out the search radius. Only Hotels that fall within 8 miles from the city center will be shown.
Choose Your View
6First Class
Crowne Plaza Pittsfield BerkshireBerkshire Common, One West St
Pittsfield, MA 01201
179 Rooms

Multi-story Hotel, guest room amenities for business or leisure travelers; convenient downtown location, minutes to attractions....

Commission: 10%$129-$400(USD)
DetailsView on Map
6First Class
Jiminy Peak Mountain Resort37 Corey Rd
Hancock, MA 01237
200 Rooms

Modern condominium style resort with ski-lodge atmosphere and massive stone fireplaces located at the base of Jiminy Peak....

Commission: 10%$129-$239(USD)
DetailsView on Map
6First Class
Wyndham Vacation Resort Bentley Brook1 Corey Rd
Hancock, MA 01237
55 Rooms

Condominium Ski Lodge, modern guest amenities; located at the base of Jiminy Peak....

Commission: 10%$399(USD)
DetailsView on Map
3Superior Tourist Class
Econo Lodge Pittsfield16 Cheshire Road
Pittsfield, MA 01201
59 Rooms

Two story Motor Inn with modern guest facilities; located near the intersections of 9E and 8N....

Commission: 10%$89(USD)
DetailsView on Map
2Tourist Class
The Spring's Inn Hotel94 Route 7
New Ashford, MA 01237
40 Rooms

Motor Lodge in country setting, midway between Pittsfield & Williamstown (10 miles from both)....

DetailsView on Map
Berkshires Shirakaba Guest House20 Mallery Road
New Ashford, MA 01237
2 Rooms

This 2 room property, built in 1999......

DetailsView on Map
Mount Greylock Inn6 East Street
Adams, MA 01220
4 Rooms
DetailsView on Map
Hotel on North, Pittsfield297 Main Street
Pittsfield, MA 01201
45 Rooms

This 45 room property, renovated in 2015......

DetailsView on Map
Vacation Village in the Berkshires276 Brodie Mountain Rd
Hancock, MA 01237
296 Rooms

This 296 room property, renovated in 2012......

DetailsView on Map
Weathervane Motel475 S Main St
Lanesboro, MA 01237
DetailsView on Map